Love is a Losing Game
by joyousbrokenthing
Summary: She could no longer remember when either of them decided to play, but now neither of them could stop until there would be one clear winner. She pushed, and he pulled, and they followed closely to these unspoken rules. One of which....she just broke. C
1. Chapter 1

Chuck Bass was not one to play gentle. So when the fragile girl beneath him started whimpering, he only pushed harder. His mouth found hers. Hot, rough kisses stopped the whimpering and her breathing sped up. She was in pain, he could tell, but Chuck Bass would not stop until both parties were in pure exstacy, he always made sure of it.

"Ohhhh God..." She moaned, "CHUCK!"

That was that. One final thrust and her body was shaking in pleasure. He fell beside her, body tired, both breathed heavily. She rest her head on his shoulders, arms wrapped around him.

Chuck Bass was not one for cuddling. He got up rather quickly and threw on his boxers. With a lit joint in one hand, he poured himself a glass of whiskey on ice from across the room. He looked back at his bed, the stunning blonde girl now laid upwards, smirking at him dangerously, asking for more.

"Leave."

"What?"

"Get out of here."

"You've got to be kidding-"

Chuck Bass was not one to repeat himself. He didn't respond. Rather, he took his drink to the next room and threw himself onto the couch in the spacious suite. He could hear muffled swearing as she looked for her clothes in the next room.

"You're an asshole." He heard her yell, rather loudly.

He just smirks and takes another sip. What was new?

Suddenly the door swung open.

He stood up and turned quickly to see the stunning brunette just burst through the room. He smiles at her sincerely as she takes off her coat. The door closes abruptly behind her and she makes her way towards him, stopping dead in her tracks as the tall blonde girl, Amber? Amanda, was it? entered their view.

She lets out a small chuckle as if she's amused and changes direction to walk directly to the bar to fix herself a drink. The confused blonde girl just looks from Chuck Bass to the brunette. Shaking her head, she rolls up her knee socks, slips on her boots and quickly walks out the room in uncomfortable silence.

Once the door slams shut Chuck Bass shines his signature smirk and raises his glass before chugging the rest of his whiskey. She does the same.

"What's her name?" She asks.

"Amber." He replies honestly, his ridiculous smirk growing wider."Or was it Amanda?...You know it doesn't matter, Blair."

She throws herself graciously onto the arm chair, crossing her legs and circling the rim of her glass with her perfectly manicured fingers.

"True" she replies, taking another sip.

He takes a seat on the end of the couch near her, caressing the skin on her legs with his warm hands, sending shivers down her spine.

She takes a moment before pushing his hand away.

"Not after you've touched" her eyebrows furrowed "Am-"

"Never stopped you before." He shoots back before she could finish.

"Urgh, you're disgusting." she stands up and grabs her purse.

"Wait, I'll go clean up, wait for me?" He asks as innocent as possible.

She looks down at his disgruntled face, almost begging in desperation.

She nods quietly and sits back down as he walks towards his bathroom.

"Sure you don't want to join me?"

"Can't, I have dinner with Nate in an hour." she replies automatically, eyes on the phone in her hand.

Realizing her mistake she turns to search for his reaction, he only shakes his head and closes the door behind him.

She waits to hear the shower turn on before sighing deeply falls back into her chair.

She takes another shot at her drink and tries to clear her head. Here she was in Chuck Bass's suite, once again, for god knows how many times now. Playing his game, their game, with their unspoken set of rules.

She could no longer remember when either of them decided to play, but now neither of them could stop until there would be one clear winner. She pushed, and he pulled, and they followed closely to these unspoken rules. One of which...she just broke.

She would never mention Nate. This rule was Chuck's, of course. And he would continue to sleep with whoever he pleases.

Blair's set of rules were just as selfish. She would come and go as she pleases, he would never ask about Nate and no matter who he was sleeping with, she always came first. All of which he happily obliged.

None of these rules were ever spoken, but somewhere along the lines, they understood. And they played along wIllingly, and sometimes unwillingly,

Blair picks up a pair of panties under the coffee table and throws them across the room in disgust. She could remember the first time she found him with someone else. Chuck was her escape. He was her escape from her chaotic, stressful, picture perfect life with Nate. Then one day she had found him in a compromising position with some trashy whore in his room. Suddenly her escape caused more pain than what she had ran from in the first place. So she ran again. She ran out of the room crying, tears streaming as Nigra Falls. He reached her before she could reach the end of the hallway. And he took her back into his arms. And they stood there. She, fully clothed and he wrapped loosely in a robe, both naked, vulnerable. She was buried into his chest and he held on for dear life. And he waited. And she cried. And waited. And she left. No words were spoken. None were needed.

She returned, of course, she always returned. It was awhile before the second time she had found him with someone else. And the third time. And the forth. And soon she lost count. And each time the tears were less, the shock wore off and rule #2 was set in motion. They never talked about it.

So she continued to play. She couldn't stop. She wouldn't. Not until there would be one clear winner.

Her phone buzzed in her hand and woke her from her deep thoughts.

NEW MESSAGE

She flipped it open.

I have to cancel. Something came up. Call you soon. 3 Nate

The bathroom door open as the hot steam escapes. Chuck stood before her, one hand on the towel around his waist, the other held onto the back of his neck.

Perfect. She thought.

She turned off her phone and threw it aside.


	2. Chapter 2

Chuck Bass was not one for jealousy. But he could not keep his eyes of the brunette dangling off the arms of his best friend. She glowed in the room full of over privileged youth. Her hair held up loosely, but not a single strand out of place. Her black cocktail dress clung onto her body tightly but conservatively, leaving much to his imagination. He stood silently in the corner, champagne flute in one hand and a gorgeous blonde model on the other. He grinned as she stole looks his way and started kissing his blonde date aggressively. In the corner of his eyes, he could tell she was watching.

So he waited. She would come. She always did.

As if clockwork, his phone vibrated in his pants.

NEW MESSAGE

Hallway. Now. – Blair

"I'll be right back." He says to the blonde before carefully slipping out of the party.

"Well, well, well…"

"Shut up Bass." Blair rolls her eyes.

It had been three days. 72 hours. She hadn't touched him for nearly 4320 minutes. She had told herself she would stay away. For good. But for christ sake, here she was. With Nate nearly a room away. Chuck Bass was her drug. And she just relapsed.

Her mouth found his aggressively and her hands grabbed at his shirt.

Her dress was quickly slipped off her shoulders, barely onto her body any longer.

"Not here." She whispers, in between kisses.

She shoves him quickly into the elevator and pins him against the wall.

She couldn't remember the last time she lasted this long without him.

He quickly pushes for his floor and dove back into her kiss. His shirt was unbutton, bowtie on the ground, belt unbuckled, and pants unzipped. Her dress was barely clinging onto her body. They struggled to keep their clothes on.

The spun each other around in circles, lips attached.

"Come on, Waldorf, behave yourself." He pants heavily, "We're almost to my floor."

She closes her eyes tightly as his mouth found her neck once more, he could feel her head shaking profusely. He stops for a second to look at her. She smiles sweetly and just nods. He presses he emergency stop button. The elevator came to a halt.

Her dress slips onto the floor as he places hot wet kisses onto her neck. She pushes his shirt back, sliding it off his arms and then struggles with his pants.

He grins mockingly. Her panties came off in seconds and her legs were wrapped around his waist, back pressed against the wall.

Blair Fucking Waldorf. Having sex in an elevator. With Chuck Bass, nonetheless. Classy.

Chuck didn't know hell was freezing over so soon.

15 minutes later they were back into the party. She was back at Nate's side and he was sitting at the bar. They stole looks every so often, grinning more widely than ever.

Suddenly he felt someone sit beside him.

Looking to his right he saw a familar face, one he couldn't quite put a name too.

"Hi there," he extends his hand with a sly smirks, "I'm Chuck."

"Vanessa." she replies

"Dan's friend?" He asks, remembering the many times Serena had complained about this particular name.

She smiles, "Yes...Your party?"

He nods coyly, grinning wider.

"How about you say we go up to my suite and I'll throw you an after party?"

She takes a sip of her martini and bites the olive flirtaciously. She leans into him just close enough to whisper into his ear, "Chuck Bass throwing a party just for me? I feel honored," she purrs, "but I'm afraid I'm not your type...elevator sex isn't really my thing."

She pulls back, grinning widely. Looking from him to Blair Waldorf who was happily sitting in Nate's lap.

She noticed the smirk on his face vanished, his eyes filled with fear and intrigue.

"What do you know?"

"Oh, nothing." she replies, "Just that our precious Upper East Side princess isn't all that she's cracked up to be."

She looks back at Nate, "Poor Nate Archibald, having his best friend and girlfriend sneak around right under his nose."

"You will not tell anyone or I will destroy you."

She chuckles slightly, "Oh please, you sound like Queen B herself."

"What do you want?"

"I haven't decided yet." She grabs her drink and hops off the stool, "But I'll let you know."

She winked mockingly and walks out of the party. Chuck chugs the rest of his drink and looks back at Blair and Nate.

He wanted to throw up.

A/N: Glad everyone liked the first chapter. It was written as a one shot and chapter 2 was written seperately but I thought what the heck and decided to make this a full length story. This is my first fanfic in about 3 years, so character development and writing is very rough. Sorry. Reviews and positive critque highly encouraged. :


	3. Chapter 3

She questions the unknown number on her phone and decides to pick up on the thrid ring.

"Hello?"

"Vanessa..." the low voice replies

"Who is this?" She asks, curiously.

"Chuck Bass, have a moment?"

"How did you get my number?" She was intrigued.

Chuck Bass did not want to mention the awkardness and accusations that ensued by asking Serena.

"Money will get you everything," he lies.

"What do you want, Bass?" she asks, clearly annoyed.

"To see you, tonight. Drinks? 7 o'clock?" He demands

She could envision his smirk on other side of the phone.

"Look: if you want to shut me up about your little secret, you don't have to worry-"

"I'm not. No worries."

"What? Is this a date?" She sneered.

"I'll pick you up at 7."

"Make that 8." She responds, after a quick moment of hesitation.

"As you wish."

Vanessa Abrahms slowly closes her phone shut, completely in disbelief at the events that just had happened. She knew Chuck Bass was a dangerous person to cross and Dan will surely un upset she's interferring with the filthy rich, no matter how hypricritcal it was.

But she was curious. And she could surely handle herself. This was going to be an interesting night.


	4. Chapter 4

Like clockwork, a shiny limo appears in front of Vanessa Abrahm at exactly 7 o'clock.

She hesitantly hops in as the driver opens the door for her.

Chuck Bass was sitting in the corner, scarf clad and all.

"Hello, gorgeous" he purrs and smiles, raising his glass before taking a drink.

Vanessa rolls her eyes as she situates herself a seat away from him.

He quickly hands her a drink.

"Let's not beat around the bushes," she states "don't waste my time, what do you want?"

"To be friends." he replies casually, grinning wider.

Unbelievable.

"I'm not going to tell anyone."

"I'm not worried." he lies.

"Like hell you're not." she tilts her head back, downing her champagne, "It just doesn't make sense."

"I'm telling you, I'm not worried."

"Not that." she looks him straight in the eye, studying him closely, he was so hard to read.

"Why would the squeaky clean Queen B Blair Waldorf cheat on Nate Archibald for someone like-"

"Like me?" he asks, smile wiped from his face.

She smirks.

After moments of silence Vanessa realizes that Chuck Bass, for the first time she's seen him, was striped of the hideous womanizing, manipalitive, overprivledged mask he hides behind. He looked even, dare she say it, vulnerable.

He turns away and takes a deep breath.

"You care about her, don't you?" She asks sincerely.

"Please." he responds, chuckling softly.

"You wouldn't waste your time trying to shut up some girl from Brooklyn if you didn't."

He didn't respond.

"Face it, you care. And I don't. Whatever the two of you have going on, it's none of my business. So you don't have to worry." she says "I'll pretend it never happened."

He gave her a questioning look before smiling genuinely.

"Thank you."

"Look, I understand more than anyone what it feels like to have feelings for someone you're not supposed to. It's not easy."

She smiles and grabs for her purse as the limo pulls to the side of the busy street.

---------------------------------------

Two days later Chuck Bass found himself at another useless charity event. Chuck makes his way to the bar and was automatically greeted with a whiskey. He looked around the room. As usual Dan looked out of place, Serena smiled like a fucking idiot, Kati and Iz were on there phones and Blair and Nate glowed like the perfect golden couple. They were holding hands and pressed together. Their outfits complimented the others perfectly

Everyone looked at them as if they were UES's own Brad and Angelina. Chuck scoffed. If only everyone in the room knew that while Nate was sound asleep last night Blair Waldorf was in his suite purring and moaning Chuck's name. He smirks and takes a sip of his whiskey.

"These events are painful, aren't they?" Nate asks as he approaches Chuck, patting Chuck on the back "I could really use a smoke, wanna go?"

Chuck turns around from his bar stool only to stop moving as Eleanor and Mr. and Mrs. Archibald approached them with Blair trailing behind.

"Nate," Eleanor says "Your parents and I were just talking about what you and Blair would do next year. Seeing as how you two are inseperable they might have to combine Yale and Dartmouth."

Blair's face lit up. Nate smiled akwardly. Everyone laughed. It was stupid comment. So fucking lame, Chuck thought.

Chuck rolls his eyes and slips away as the laughter continued ringing behind him. He didn't care to turn around to see Blair eyeing him suspiciously.

Chuck slips onto the balcony and closes the door behind him. Grabbing his phone he scrolls down to the bottom and hits send before thinking twice.

"Hello?"

"Can we meet? Please?" He was desperate. He was sure he sounded so too.

"Um..." Vanessa hesitates, Chuck Bass did sound desperate "Sure. I'm at home if you want to-"

"I'll be right there."

Vanessa closes here cell phone and sighs. What the heck was she doing?

Within minutes Chuck Bass pulls up once again in his shiny limo. Vanessa opens the door before the driver gets to her. Chuck was staring back at her, quite surprised that she was standing there looking at him.

"Get out of your car."

"What?"

"You have legs Bass, let's take a walk."

He smiles, shakes his head and slowly climbs out. Vanessa closes the door behind him and leads the way down the busy New York street.

They walk togther in silence for a good amount of time before reaching central park. She stops in her tracks.

"Is there a point to this?"

Chuck looked at her dumbfoundedly trying to search for something to say but he had no idea why he called, why he asked her to meet him or why the hell he dismissed his driver and was walking around Central Park aimlessly.

"I-" he sighs "you said you understood more than anyone."

"I see." Vanessa nods and continues walking

Chuck catches up to her, "You were right. It's not easy."

"Of course I'm right."

"I can't fuckin do anything without thinking about her. I can't stop screwing other girls just to try to forget her, I can't stop dreaming up ways to murder my best friend for christ's sake." Chuck blurts frustratedly.

"Does she know this?" Vanessa asks.

"No..." he replies quietly.

"How come?"

"Because," he replies, like it was an actual answer.

Vanessa looks at him questionly.

"I'm _Chuck Bass_." he finishes.

Vanessa pauses and looks at him, then she bursts out laughing like it was the funniest thing she's heard all day. Chuck ends up laughing also. They continue their walk talking about all things forbidden love. It was such an odd situation for both of them. Being with the least likely person they'd be caught dead with, revealing to each other more than they ever would a close friend. Chuck Bass felt like for the first time in ages a weight was lifted off his shoulders.

They both failed to notice the cell phones snapping away at the odd occurence.

--------------------

Blair Waldorf sat at her laptop scanning Gossip Girl. She read the headline over and over again, afraid she'd misread.

"WTF? C and V?

SPOTTED: C and V in Central Park strolling like they've known each other for decades. We're just as surprised. Has this new romance been brewing right under our noses? And since when does Chuck Bass stroll through Central Park? Is he changing his ways? S and D, anyone? We'll keep you posted.

xoxo

Gossip Girl"

Blair read it again and again. There had to be a hell of a good explanation.

A/N: Sorry for the very little Blair lately. It's hard to get into her head. The story finally has a direction and I'm very excited about it. Hope everyone is still interested. And don't worry about Vanessa. Still completely Chuck/Blair.


	5. Chapter 5

**Love is a Losing Game**

**Chapter 5**

Chuck Bass was suddenly woken by a hard hit to the head with a pillow.

"What the hell?" He grumbles as he sat up in bed.

"Wake up Bass."

Blair Waldorf stood beside his king size bed with a pillow in hand. She was dressed in a simple black dress, heels to kill and her sequined purse clutched tightly. She looked very impatient. Blair sat down beside him and threw her phone at his chest.

Chuck Bass looked at the screen displaying the flashy headline on Gossip Girl "**SPOTTED: CHUCK LOSES JACKET AFTER WALK WITH VANESSA. Is it serious?" **He scrolls down to see pictures of himself and Vanessa with smiles on their faces. Vanessa was wearing his jacket. His mind thought back to the cold breeze of the previous night and the oddly kind gesture he offered. But to make it onto Gossip Girl? The rumor mill must be running low on stories lately.

"Anything I should know?" She asks impatiently, folding her arms.

Chuck smirks and hands the phone back to Blair.

"Since when do you care who I see?"

"I don't." She replies coldly, "It's just...I didn't know your taste was so bad. But then again, you'd bang everything in sight, wouldn't you?"

"You included?" He grins, tracing circles on her arm.

Blair pulls away quickly and walks away from his bed.

"You're disgusting," She scoffs, "As if I'm not embarrassed enough by even being in your presence, Vanessa is a new record low for you."

Blair didn't understand why she was so upset. It's not like he'd even see a same girl twice anyways. With the exception of her, of course. But Blair was still taken back by the fact that he made it onto the front page of Gossip Girl looking...geniunely happy. Strolls through Central Park? That was defineatly _not _Chuck.

Chuck pouts as he throws the covers aside and stumble towards her. He slips his hands around her waist and grins.

Blair grunts and breaks away from his arms.

"Don't even think about it, I have plans this morning."

_Plans_. Chuck thought. Unspecified _plans _meant Nate.

"I'm going to remind you now since I'm sure you've forgotten," Blair calls back as she reaches the door, "your father's Black And White Party is tonight. So cut back on the drinking for a bit and _try _to look decent, alright? All our parents will be there, and I swear to god, if you make another scene-"

"You'll do what? Take me into another elevator and punish me?" Chuck teases.

Blair's face flushes red.

Chuck smiles as the door slams shut. He couldn't believe Blair actually came over to talk about Vanessa. She never cared about who he was seeing. Was she really jealous? Or just embarrassed by Vanessa? He shook off the feeling. He'd have clean up and head down to the bar if he wanted to find a date for his dad's function tonight.

* * *

Chuck walks by the front desk when a familar voice caught his ear.

"Look, no need to bother him, I'm just dropping it off here."

He turns to see Vanessa at the front desk handing his jacket over to the concierge.

"Vanessa!"

"Chuck!" She turns and smiles, grabbing the jacket back and handing it towards him, "Hey, I just wanted to drop off your jacket, which thank you, by the way. Did you see we made the front page of Gossip Girl? I hear I'm the new Dan Humphery."

He laughs and reaches for his jacket.

"Please, you're much easier on the eyes."

They share another laugh before she begins to walk away.

"Well, I'll see you later..." she says.

"Wait...would you want to attend a lovely Black And White Party with me tonight?" he asks.

"Are you kidding? Gossip Girl would go crazy...Ohhhhh, I see." She says, catching onto his plan.

"Look, I'd really appreciate the company." He offers, "And it's for a good cause...I think."

"I...I really can't. I don't have anything black...or white...or formal, in that case." she replies, as she thought about it.

"You forget who you're talking to" Chuck grins and grabs onto her arm, leading her out of the lobby while dialing away at a number with his other free hand.

* * *

"Where were you all morning?" Nate asks across the table from Blair. She was swallowing her sushi greedily.

"Oh, shopping. Needed a new necklace for the Black And White function tonight and all."

"Why don't you wear that pretty diamond one you have?"

Blair chokes on her sushi slightly before coughing it down. She takes a couple sips of water before Nate continued.

"You wear it constantly at home, but I don't think I've ever seen you wear it in public before,"

"Nate, I wore it to the Cotillion. And besides, you know I don't like to reuse accessories." She lies.

How was she going to tell Nate that she couldn't wear the necklace in public because Chuck Bass would actually know how much she cherished the gift. Nope, she couldn't tell Nate that she was afraid of the vulnerbility she felt towards the Upper East Side's residential ass. And she espeically could not explain why she felt that way. God, she hate it when she would think of one while out with the other. She understood they were best friends and all, but did her life have to be so uncomfortably cliche?

"I'm thinking tonight we could..." Nate grabs hold of her hand from across the table.

"Nate, I'm tired." She replies, moving her hand to bring another piece of sushi to her mouth.

"Already?" he asks bewildered.

She smiles sweetly and takes another sip of her water.

Typical Blair.

--------------------------------------------------------

Hours later they were gathered together at yet another charity event. The ballroom at the Palace was transformed into a dazzling function. Each table filled with the incredibly wealthy do gooders and over the top center pieces. Blair was seated at a table reserved for their inner circle. She had Nate to her right and Serena to her left. Life couldn't be more perfect, she thought to herself, scanning the room for the brown haired trouble maker. Dan was on the other side of Serena, followed by Kati, Iz, and their nameless dates. The two seats across the table was still empty. Blair couldn't wait to see what ridiculous bimbo Chuck would bring tonight.

As the lights were dimming and the spotlight focused onto the podium of the stage, the ballroom doors swung open. Chuck Bass, hand in hand, with his mystery date walked slowly towards their table.

As they got closer, everyone's jaw hit the ground.

"Vanessa?!" Blair and Dan cried out in unison.


	6. Chapter 6

**Love Is A Losing Game**

**Chapter 6**

All eyes were on Vanessa as she sat down next to Chuck Bass.

"Vanessa? What...what-what are you doing here?" Dan asks in that akward nervous way of his.

"Dan." Serena hushes him as the presenters on stage started their introduction about the benefit.

The tension at their table could be cut with a knife. Blair rips apart her breadstick violently as she stared Vanessa down. Dan's jaw was still on the ground as he looks from Vanessa to Chuck. Vanessa fumbles with her napkin in her lap nervously as Chuck just smirks at the akward situation that was bringing him twisted pleasure. He grabs onto Vanessa's hand from under the table and squeezes tightly, reassuring her she's not out of place.

The applauses around them uproared and the lights were once again brightly lit. Everyone around the room started moving around, mingling with one another yet the youthful 8 at their table sat uncomfortably still.

"Vanessa, you look lovely." Serena says excitedly, breaking the silence.

"Thanks..." She replies nervously.

Blair scoffs a little too loudly causing Nate to give her a look of warning that she shrugs off.

Blair does a double take on Vanessa. She did look lovely. Her white strapless, Valentino sequined dress was sparkling on her body. And dear god, that diamond Tiffany's necklace around her neck was blinding. Chuck's doing, she was sure. Blair rolls her eyes and continues ripping apart her breadstick, throwing the pieces back on her plate.

"Vanessa, a word?" Dan demands, gestering towards the door.

She looks at Chuck apologetically and follows after Dan.

"What the hell Chuck?" Blair asks bluntly.

"What?" He grins, "Jealous?"

Blair's face flushes red and she looks at Nate with concern. Thank god her boyfriend was the most oblivious person on earth.

"As if!" she snaps, "I'm going to the bathroom."

She kisses Nate on the cheek before removing herself from the room.

Within seconds Chuck checks his phone with a wide smirk.

NEW MESSAGE

Hallway in 15. -B

* * *

"Vanessa, what are you doing with Chuck Bass?" Dan asks Vanessa impatiently as they reach a quiet corner. 

"I'm attending a society event with him, hardly something to get your panties in a bunch, Dan."

"Society event? Who are you?"

"Oh, so suddenly you can be fit right in, but I can't?"

"That's not what I meant. This is Chuck Bass we're talking about."

"What about him?"

"He only wants girls for one thing, he's a douchebag Vanessa-"

"I'm not sleeping with him, if that's what you're implying."

"Then what are you doing with him?"

"It's none of your business." She replies, staring back at him intensely.

There was no way in hell Dan would understand that she actually enjoyed Chuck Bass's company. Hell, even she couldn't comprehend it. She walks away angrily to find Chuck.

* * *

"Just can't keep away, can you Waldorf?" He teases, brusing the hair out of her face. 

"Explain to me again why you're stooping to Serena's level of awful taste?"

"Again, jealous?"

"You wish. And **never** flirt with me so obviously in front of Nate again, are we clear?" She kisses him passionately, slipping her hands under his shirt, "I might not be able to control myself."

Blair gasps as the sudden coldness hits her as he pulls away.

"As much as I love dirty affairs with you in empty hallways, I wouldn't want to keep my date lonely. That'd be impolite." He winks and heads off towards the ballroom. Smiling to himself at the thought of Blair Waldof still standing behind him, flabbergasted. Chuck was overwhelmed with this new satisfaction of making Blair want him. And boy, did she want him. He was sure of it.

Chuck walked back into the ballroom only to be cornered by Dan. Serena followed closely behind.

"Bass, stay the hell away from Vanessa, okay?"

"Don't be too concerned, Humphery, your girlfriend might get the wrong idea." He smirks and looks at Serena, who looked like she was ready to fall apart.

Chuck slips away as Dan turned to Serena.

God damn this was a good night, Chuck thought to himself. All he needed was a drink to make the night even better.

* * *

Vanessa hurried down the hallway back from the ladies to room to hear her name being called. She turns around to see Blair Waldof smiling sweetly at her. 

"Chuck is looking for you." she says.

"Is he?" Vanessa asks, skeptical of Blair.

"Yeah, he got sick of the party. He's up in his suite, I can take you." Blair offers, hooking arms with Vanessa and walking rapily down the hallway.

They step into the elevator and Blair pushes for the top floor.

"Isn't his room the penthouse suite?" Vanessa asks, pointing to the big letter P right below the top floor.

"No," Blair replies, "The top floor is all his. His dad renovated it just for him. It's over the top, but that's Chuck for you."

Blair chuckles akwardly. The elevator door swung open and Blair once again drags Vanessa down a oddly white empty hallway, pushing a large metal door open with all her might. Blair shoves Vanessa out before closely the door quickly.

"Hey! Let me back in!" Vanessa shouts, "What the hell Blair?! This is the roof!"

"Oops, is it?" Blair asks, "Guess he lives in the penthouse suite afterall."

"Fuck, Blair," Vanessa screams, pounding on the metal door, "This isn't funny. It's fuckin cold out here."

"Now don't you wish you had a little more on than that skimpy dress?" Blair laughs before continuing, "Stay away from my friends, Brooklyn. I may have to deal with Humphrey for Serena's sake but one charity case is enough."

"Blair, I'm so going to kill you!!" Vanessa cries desperately.

"You have no idea who you're dealing with." Blair replies, before walking away.


	7. Chapter 7

**Love Is A Losing Game**

**Chapter 7**

"Have you seen Vanessa?" Chuck inquired as he wandered over to join a group of his peers, conversing in the middle of the ballroom. His gaze and question were directed solely to Nate, choosing to ignore the rest of the young socialites surrounding him, including the triumphant face of one Blair Waldorf. Unfortunately for him, before his best friend could form any sort of a response, she decided to but in and offer up one of her own.

"Did you happen to lose your date, Chuck?" She was intelligent enough to make her voice sound sugary sweet, inoffensive to all that didn't know her well enough. What gave her away though, at least in his eyes, was the smirk that her red-stained lips had formed while she ridiculed him from behind her innocent question.

"If I had brought her here, I certainly wouldn't have let her out of my sight. I imagine that she feels quite lonely without you by her side and uncomfortable, seeing as she hasn't ever attended a party like this." Blair continued on, her voice embracing a chastising and slightly mocking tone.  
He couldn't help but feel slightly impressed at her dramatic display and allowed himself to silently praise her for her efforts. However, he had other matters to attend to so he allowed himself to study her expression for only a second before addressing Nate.

"Nathaniel, I believe I heard that the Captain is presently looking for you." Chuck said, looking at Blair out of the corner of his eye as he took a sip of his champagne.

A look of pure exasperation settled itself over Nate's face and he heaved a sigh before nodding and reluctantly making his way into the crowd. With Nate out of the way, the opportunity to question Blair in private presented itself. Chuck quickly excused himself and roughly taking a hold of her upper arm, steered them out of the ballroom and into the deserted hallway, ignoring her cries of protest. After ensuring that they were indeed alone, he none to gently slammed her into one of the closet doors.

"What exactly did you do Blair?" His haze had darkened to a near black, sparks of anger dancing in his eyes. A look of fear flashed across Blair's face, but within a moment she had pulled herself together and yanked her arm out of Chuck's vice-like grip.

"Let go of me, Bass." She shot back, pure venom lacing her words. "I didn't do anything."

"I know you so much better than you think, Waldorf. Now tell me what the hell you did to Vanessa or God help me I'll…" Chuck's rant would have gone uninterrupted had it not been for the unexpected and thoroughly annoying presence of Dan Humphrey.

"What about Vanessa?" Dan had somehow managed to put himself in-between Chuck and Blair, with his arms folded and his face already holding an expression of suspicion and anger. "Where is she? What'd you do Bass?" he inquired roughly, going so far as to shove Chuck into the opposite wall. Serena watched the confrontation in silence, moving only to usher Blair out of the corner.  
Chuck shot Dan a dark look before turning his back on him and grabbing a hold of Blair once more.

"Blair, tell me where she is or I'll let everyone know your dirty little secret." Chuck threatened, his voice coming out in a low hiss. "I might even mention it to Nate."

"Mention what to me?" Nate appeared at Chuck's side, an air of puzzlement enveloping him as his gaze landed on a distraught Blair, her eyes filled to the brim with unshed tears.

"What the hell is going on, Chuck?" Nate asked as he pulled Blair into his arms and began to mutter comforting words into her ear, hoping to calm his near hysterical girlfriend.

"I suggest that you ask Blair about Vanessa's whereabouts since she seems to know everything about everybody these days." Chuck hissed, his glare making Blair squirm. She then tore away from Nate's arms and proceeded to straighten out her mussed attire.

"She wanted some fresh air." Blair replied, her voice an even tone. "I don't owe anyone an explanation for that." With that said, she turned on her heel and stormed away with Serena trailing after her.

"What the hell does that mean?" Dan asked impatiently as he struggled to keep his hands from wrapping themselves around Chuck's neck.

"Fuck." Chuck mumbled, Blair's cryptic explanation becoming all too clear to him. He made a mad dash for the elevator with Dan and Nathaniel on his heels. Pushing the button for the top floor, Chuck tapped his foot with irritation as he watched Dan study him.

"Nothing better have happened to her or I'll-"

"You'll what?" Chuck spat out. He had quite a lot more to say to Dan Humphrey but the door flew open before he had the chance. The trio ran quickly to the very end of the hallway and proceeded to open the door to the roof. The cold night air whipped at their faces but that did nothing to deter Chuck as he ran towards a huddling figure, seated on the corner of the roof. Vanessa Abrams was rocking herself back and forth, her arms the only thing to offer her heat. On her face were tear marks but her crying had ceased.

Chuck made his way over to her, removing his jacket in the process and draping it across her petite and shivering figure. He pulled her into his warm embrace and only hugged her tighter as she began to convulse. Observing the intimate moment, Dan decided to intervene, offering to drive her home.

"Actually that's unnecessary, Humphrey seeing as I will be escorting Vanessa home." Chuck replied as he helped Vanessa stand and supported her frame as the walked back into the hotel, leaving a silent Nate and an enraged Dan behind in the cold. In the elevator, Vanessa broke away from his embrace, anger clearly displayed on her face.

"Vanessa, I can't tell you how sorry I am," His voice was uncharacteristically apologetic as he attempted to explain the night's events. "Save it." She snapped, "Whatever the hell you have going on with Blair, I don't want to be a part of it. What I want is for that psychotic bitch to stay as far away from me as possible."

Her fiery words made him smile and he couldn't help but try to apologize once more. "I never thought that she would lash out at you like that," He explained, "otherwise I wouldn't have brought you in the first place."

"Why did you bring me then, Chuck? Did you do it just to make Blair jealous? Well congratulations, mission accomplished! Now we can stop pretending like you care about me at all!"

In response to his surprising reaction to her admission, Chuck Bass found himself wrapping his arms around her slight frame, drawing her as close to him as physically possible and crashing his lips into hers'. To his great shock, she neither pulled away from their embrace nor slapped him for his abrupt actions. In fact, she did quite the opposite, lacing her fingers in his hair and returning his kiss with equal fervor. Just then, the elevator doors eased open to reveal a shocked Blair Waldorf, accompanied by Katie and Iz, who somehow managed to pull out their cell phones just as the pair broke apart. Blair's expression changed from shock, to anger and finally to one of hurt.  
Putting herself together, she adopted a mask of indifference and after casting the couple a look of utter disgust, turned and began power walking towards the ballroom. Kate and Iz, on the other hand, decided to snap a couple of photos on their way out, opportunists that they are.

With a frustrated sigh and a roll of his eyes, Chuck slipped his hand into Vanessa's and lead her out of the hotel doors. His black stretch limo awaited them at the curb, and being the gentleman that he was, he opened her door and with a sincere smile bid her goodnight. After giving the driver directions to her house, he turned to walk back inside, looking less than forward to seeing the people inside.  
His mind ran through a million different ways that he could act when Blair would come find him and demand justification for the compromising situation that she had found him in. He wasn't sure what the hell had just happened but he had to be prepared for the confrontation that was sure to come his way. She would come find him. He knew she would because that was exactly what he would do if he was in her place. They were two sides of the same coin, Blair Waldorf and him. And sometimes, that scared him.

* * *

"Blair, where have you been?"

She twisted to see Nate making his way over to her and turning away for an instant, she downed her martini and forced a smile onto her face before facing him once more.

"Oh, I just went for a little walk to clear my head." She replied as she set down her drink on the counter and motioned to the bartender to keep the drinks coming.

"Like Vanessa went for some air?" Nate questioned, searching her face for some sort of explanation.

"I just don't like her, alright?" She replied, bites into her olive aggressively. "I'm entitled to my opinion!" Her words were accompanied by yet another swig of her drink.

"Blair," Nate pleaded, his hands placing themselves over hers' "I know you don't like most of the girls Chuck sees, but don't you think Vanessa's different? She seems nice enough and what you did was uncalled for! It was inappropriate for you to do that. Chuck's my best friend, after all and I want to see him with a respectable girl for once."

"Oh God," Blair huffed out, swiveling in her seat to put her hands on Nate's knee, "Is that what you think this is all about? You should know that I don't give a damn about whom Chuck decides to bed. I only did what I did for Serena's sake." Her words sounded sincere enough but she was lying through her teeth, all the same.

"For Serena?"

"Well of course, Vanessa and Humphrey have a romantic history together. Serena's been very worried about Vanessa and her involvement in Dan's life so I decided to interfere. I only did it for my best friend." It was funny how the more she lied, the easier it became.

"I'm glad you and Serena are looking out for each other again, but regardless, it was wrong of you. What if that stuff got onto Gossip Girl, I'd hate for there to be more rumors about you."

"Noted." She smiled sweetly, giving Nate a quick peck on the lips before resting her head on his shoulder. "I'm sorry that what I did upset you."

"I know you are. Well, I'm going to head home now, do you need a ride?"

"No thank you, I'm going to see how Serena's doing after all of tonight's dramatics. I'll call you tomorrow, though."

Nate nodded before waving goodbye and heading for the exit. She waited as the doors slammed shut behind him before whipping out her cell phone. Dialing a number she knows by heart, she waits patiently for him to pick up. He answers on the third ring and before he can get a word in edge wise, she interferes.

"Chuck. I'm coming up." She abruptly hangs up, without even waiting for a response. Blair finishes off her forth martini before stumbling towards the elevator. She can't help but wonder if he knew that she'd call. She wonders if he knows her that well or if she's just that predictable.

_Author's Note: First and foremost, a big thanks to my wonderful new editor Megan (Crimson-Kiss17) for doing an amazing job with this chapter. Notice the much better use of words and grammar? All her. I just supply the plot and dialogue. ; Secondly, thank you so much for all your reviews. They always put a smile to my face and encourage me to keep writing. Hope you enjoyed this update and I will try to update daily from now on. _


	8. Chapter 8

**Love Is A Losing Game**

**Chapter 8**

As soon as the doors parted, she stumbled out of the elevator and into the empty hallway. Counting the door numbers as she passed them by, Blair tried desperately to remember which one was his.

"Is it 4567 or maybe 7654?" she mumbled drunkenly, leaning against the walls to support her petite frame.

Making the executive decision that his room number was indeed the former, she staggered down the corridor, stopping only when she reached the door marked 4567. Using her small fists as a means to be granted access, Blair began to pound violently on the wooden door, swaying from side to side as she did so. Within moments, swearing could be heard from inside the hotel room and she giggled at his colorful choice of words. The door soon swung open to reveal Chuck in a tight black t-shirt and a pair of gray sweatpants with a none too pleased expression painted across his handsome features. In one swift movement, he ushered her inside and closed the door, all the while praying that she hadn't awoken any of his neighbors. He reluctantly turned to find an intoxicated Blair Waldorf pressed up against him with a silly smile playing across her lips.

Before he could reprimand her for coming up to his hotel room, drunk no less, she threw her arms around him and attacked, laying hot, open-mouthed kisses on his neck.

Pleasure seeped into his senses, her ministrations causing his mind to fog up at an alarming rate, leaving very little room for rational thought. "Blair..." He attempted to push her away and separate their bodies, but even as smashed as she was, she anticipated his hesitance and only moved to close the gap between them once more. Pinning his muscular frame against the wall, she let her hand slip under the hem of his shirt, letting her fingers graze the muscles beneath in rhythmic strokes. Her eager hands explored his warm skin, never satisfied until she had touched him in every place possible. Despite the bliss that she was inducing, Chuck knew that he could never take advantage of her in such a disoriented state. If there was going to be anything at all between them, it would occur when she could actually stand up straight, without assistance, for more than ten seconds.

"Blair, you need to stop this!" He pleaded desperately while using his hands to gently push her backwards.

While slipping out of the corner that she had skillfully backed him into, his chocolate gaze begged with her to hear reason. In response to his rejection of her advances, her doe eyes began to fill with tears as she turned her back on him. Immediately a wave of guilt crashed over Chuck as he observed her breaking down before him, with her head in her hands and her frail body convulsing with sobs. Chuck couldn't stand to see someone so close to his heart be in such pain so he reached out to draw her into his arms. While his intention was to offer her purely platonic comfort, Blair had other ideas. Running into his open arms, she titled her face upwards to meet his lips in a passionate kiss. Even with willpower, he was powerless over her and didn't even think before darting his tongue out to taste her. He was met with the flavor of martinis, strawberries and something uniquely Blair. Letting out a low primal growl, he took charge over their little dance and proceeded to pin her arms over her head. Wandering hands and skillful tongues stumbled over to the king size bed with Chuck gently lifting Blair's body and depositing her onto the mattress. His body settled itself comfortably over her while she fumbled with his belt buckle, all the while maintaining eye contact. She continued her task while he took the opportunity to rid her of her evening gown. Between the trail of hot kisses that he deposited on her collarbone, Chuck managed to mutter out a command that would end it all.

"Leave Nathaniel." He whispered, stopping his ministrations to look directly into her wide eyes. She met his gaze with defiance and said nothing, choosing to instead sit up to capture his lips in yet another steamy kiss. Chuck knew all to well what she was trying to do, and he was having none of it. Breaking the kiss he tried once more, aggression lacing his order. "Leave him."

Blair's eyes once more began to fill up and she turned her head, refusing to meet his pleading gaze. And just like that, he removed himself from the bed, walking over to the windowsill to catch his breath and straighten his clothes.

Slipping back into her gown, Blair didn't dare to look his way, fearing the pain that she knew would be etched across his face.

"It's over." He mumbled, keeping his face angled away from her, "The next time you decide that Nathaniel isn't good enough, that you need something more, don't come looking for me. I won't be there to catch you when you fall from that high pedestal of yours'." He turned to meet her gaze only to see a flash of skin as the palm of her hand connected with the side of his face. In a blur and the sound of a door slamming shut, she was gone. With a nod of his head, he headed for the alcohol cabinet.

* * *

"Blair? Honey, what's wrong?" Lily Van Der Woodsen closed the door behind a tearful Blair Waldorf, who had unexpectedly shown up at her doorstep.

"I'm sorry, I know it's late, but is Serena home?"

"She's in her room, just go right in." Lily replied, "I'll call your mom and let her know that you're here."

Blair nodded her thanks and made her way up the winding staircase and into Serena's room.

"Blair! Oh my God," Serena quickly threw her arms around Blair tightly, immediately noticing the distraught state of her best friend. "Are you okay, sweetie?"

Blair started crying again, sobs wracking her frame as she returned the blond's comforting embrace.

"He-" She mumbled in between sobs, "He said-"

"Shhhh, Blair it's okay." Serena began to rub her back, whispering soothing words into Blair's ears. Helping her over to the bed, Serena proceeded to ease Blair down, pulling the covers over her still shaking frame. Turning off the light, Serena couldn't help but wonder what or who for that matter, could have caused Blair to work herself into such a state. Normally Serena would have assumed that Nate had done something idiotic or thoughtless, but this time she dismissed him as the cause. Blair Waldorf had never cried so hard over Nathaniel Archibald in all the time that they had been together. No, this "he" that Blair spoke of was of far more importance to Blair, perhaps more than even Blair herself would admit.

* * *

"You want to tell me what happened?" Serena asked Blair as she entered her bedroom with a platter of waffles and pancakes. Blair was changing into a pair of Serena's jeans that were way too long for her petite frame and an old vintage Led Zeppelin t-shirt. Blair crinkled her nose at her reflection, not used to such attire.

"Yum! Waffles." She reached for the plate, ignoring Serena's questions altogether.

"Blair..." Serena chastised, pulling the plate out of the other girl's reach. She wanted answers and she wanted them now.

"Look, I better get home. Everything is fine. Drop it, okay?" Blair flashed her an innocent smile, retrieving last night's clothes from the dresser.

As the door closed behind an oddly cheerful Blair Waldorf, Serena Van Der Woodsen dropped onto her bed, sighing with frustration at the stubbornness that was her best friend.

Just as Serena stood up to finish off her breakfast, an object caught her eye. Blair's cell phone had been left behind, forgotten on Serena's nightstand. Curiosity peaked; Serena reached over and retrieved the cell phone, deciding that a little peek couldn't hurt. After all, the reasons behind Blair's hysterics could be hidden within the confines of the phone. Flipping it open, a box opened up to inform her that Nate had left a message, asking Blair to go out to lunch that very afternoon. Serena ignored this; the message only proved what she had surmised already, that Nate and Blair were on good terms. Exiting the message, she went on to explore the rest of Blair's messages, all which came from one Charles Bass. Reading all of them, Serena went on to put together all the pieces of the puzzle. Blair Waldorf and Charles Bass, who would have thought? Mind still reeling with this new discovery, the door flew open once more to reveal a frantic Blair, searching for her forgotten phone. As Blair's gaze latched onto Serena with her cell phone in hand, the dam inside her broke.

"Whatever we had together is over, okay?! I know what you're thinking, how could I ever be with him, Chuck Bass, a complete and total asshole! But there isn't anything between us anymore, he ended it." The truth of her own words finally sunk in and Blair slid to the floor. Serena didn't even question the ordeal that had been hidden from her, she just walked over and sat next to Blair, wrapping her arms around her once more.

"You know, this is all Vanessa's fault! She appears out of thin air and suddenly he doesn't want me anymore. She's from fucking Brooklyn for God's sake!" Blair ranted, as if her words made actual sense and formed a decent argument. Serena only nodded.

"It's for the best, you know." She whispered.

"I know." Blair answered, hoping that maybe saying it out loud would make it true. "I look absolutely horrible, don't I?" She muttered, sitting up and analyzing her reflection in the mirror. Again, Serena nodded before both girls exploded into laughter.

* * *

Vanessa picked up her phone for the millionth time that morning, praying for some sort of sign that last night wasn't a dream. She frowned at the empty screen that flashed before her before throwing the phone back onto the couch. She wanted to stop the stupid fluttering in her stomach; it wasn't helping in the least. Ten minutes later the phone began to ring, sending her dashing over to the couch to answer the call.

"Hello?" She answered nervously, waiting for a certain voice to answer back.

"Vanessa, how...how are you?" Definitely not the voice that she had been expecting.

"I'm alright Dan." She rolled her eyes, _now_ he decided to call.

"Listen, I feel like I should apologize for yesterday. Serena's friends can be intimidating, and I guess a tad cruel but Serena feels really bad about what happened. Really, she feels awful…" Vanessa let out a scoff as he rambled on about his precious girlfriend and her sympathetic feelings. "Now I know that you don't want me to interfere, but you just have to be careful about…"

The ring of her doorbell interrupted his last sentence and she was all too grateful for the timing.

"Dan, hold on." She unlocked the door and opened it to reveal a slightly flustered but nonetheless, devilishly handsome Chuck Bass. And with an impressive bouquet of flowers in hand, to boot. She felt the blood rushing to her cheeks as she ushered him inside.

"Chuck...what are you doing here?"

"Wait...Chuck?" She heard Dan question loudly on the other side of the phone. Annoyed with his presence, she shut the phone and turned towards her unexpected guest.

"I would say that I happened to be in the neighborhood but I think we both know I don't wander anywhere near here." He replied smoothly, a genuine smile gracing his lips. As if he couldn't be any more charming, he held out the bouquet and placed a peck on her cheek.

"For the lady of the house." She shuddered to think how red her face was at this point.

"So..." She mumbled nervously.

"I hope you're willing to continue this awkward conversation over lunch." He teased, a sparkle in his eye and he watched her shift from one side to another.

"Chuck, last night was…"

"Not fun, I know. For that, I apologize."  
She smiled as her heart began to flutter again. Stupid butterflies.

"But Blair-" She questioned, nervously waiting his answer.

"Blair who?" He smirked, "Now what about lunch?" She rolled her eyes and nodded hesitantly, reaching for her coat as he opened the door.

Chuck couldn't keep from smiling; perhaps forgetting Blair Waldorf was easier than he originally thought.

* * *

Blair's phone began to vibrate in her pocket halfway through her lunch with Serena and Nate. She was thoroughly enjoying her boyfriend and her best friend's company so such a disruption was annoying, to say the least. Couldn't she enjoy the moment in peace? Flipping open her cell, she was greeted with a bold title. 

"**LOOKS LIKE OUR DEVIL HAS BEEN TAMED**"

She scrolled down to see the image in the elevator that had haunted her all night.

**SPOTTED (twice!): C and V making out recklessly at his dad's charity function.  
He even loses his jacket (again!) and walks her to his car? Is hell freezing over?  
Or is Chuck Bass really tied down? One thing's for sure, the Upper East Side just feels a little safer somehow.  
And word is going around that they are out together on the town at this very moment!  
I wonder what V's secret is for refining our favorite playboy?**

**xoxo,  
you know you love me**

**Gossip Girl**

"What is it?" Nate questioned, noticing her state of distraction.

"Nothing." She smiled and shoving her phone back into her bag and zipping it shut.

Serena smiled at her sympathetically, guessing that something to do with Chuck had disturbed her. The meal resumed without interference until Blair nearly choked on her water as she spotted Chuck and Vanessa entering the busy restaurant.

"Chuck, over here!" Nate shouted out before she could protest.

Blair buried her face in her hands, hoping that if she was lucky, a hole in the ground would appear and swallow her up. Forgetting Chuck Bass wasn't going to be as easy as she thought.

_Author's Note: Once again, thanks to Megan (Crimson-Kiss17) for the wonderful editing. Gossip Girl is about to start in 8 minutes so I'm going to make a dash for my television. Please review. I love to hear what you think about Chuck, Vanessa, and Blair.!_


	9. Chapter 9

**Love is a Losing Game**

**Chapter 9**

Unfortunately for Blair, the world had decided to turn a deaf ear to her little issue and no hole appeared in the polished floor. That left her with two options, she could either make a run for the front entrance and hail a cab from there or she could put her brave face on and act as though his presence didn't affect her in the least. While she preferred the former, the latter was the most polite thing to do. And she normally could have pulled off such a calm demeanor as was demanded of in this situation in a second, but in order to do so properly, she needed to first control the erratic beating of her heart.

"Nathaniel, what a pleasant surprise." Lady luck was certainly not on her side today, there was hardly enough time to compose herself.

Chuck approached the table with Vanessa at his side, his hand comfortably rested on the small of her back. Such a public display of affection made Blair's blood boil, her teeth grinding together in quiet fury as she made an attempt to avoid the couple's gaze.

"Indeed it is, why don't you two join us for lunch? It'll give us all a chance to get better acquainted." Nate spoke in total ignorance of the heated glares that both Serena and Blair were sending him, oblivious to the trouble that he could cause with such an offer.

Blair's eyes widened in shock at the words coming from her boyfriend's mouth, stunned that he would offer her a seat at their table, as if she actually belonged there. Chuck caught site of Blair's obvious distress and smirked.

"The offer is most kind Nathaniel, but I feel that after last night's events, Vanessa would feel more comfortable sitting elsewhere. Perhaps another time."

With a dramatic roll of her eyes, Blair moved her focus back onto her half-eaten lunch.

"Blair is really sorry about what happened." Nate replied, shooting Vanessa a pleading look. The last thing he wanted was for something as trivial as this to come between everyone. Too bad that Blair didn't share his opinion.

"Don't put words in my mouth, Nate." She growled indignantly, throwing her napkin down angrily and storming towards the restrooms. With a heavy sigh, Serena quietly excused herself and went to follow her best friend. Bewildered at this turn of events, Nate turned towards Chuck for explanation but was met with only air.

* * *

After Blair's dramatic scene, Chuck had lead Vanessa to a reserved part of the restaurant, away from the hustle and bustle of the main room. While she examined the menus, Chuck couldn't help but sneak looks at his cell-phone, almost willing it to ring.

Seconds later, the phone began to vibrate. His eyes darted to the screen, his breath hitched in his throat as the caller id flashed across the display.  
"That would be Blair calling, would it not?" Vanessa asked, not even bothering to look up from her menu. The torn look on his face confirmed her suspicions.

"Well go on and answer, can't keep the lady waiting." He smiled at her patience; it took a strong woman to put up with him. With a nod, he flipped open the phone and walked into the deserted hallway.

"Speak."

A huff of annoyance sounded through the cell phone's speaker.

"Do you answer all of your calls so rudely, Chuck or am I just that special?" The voice leaked through the amplifier but came more loudly from the end of the corridor. Her petite frame rounded the corner and came into view, her cell phone in hand.

"Now what is this? A sober Blair Waldorf coming to find little old me?" His phone clicked shut and disconnected the call while he leaned against the wall, arms crossed and eyebrows raised.

"Shut up Bass. I'm not here for fun and games."

"Is that right? And here I thought that's all you're in for, at least when it comes to me." She glared at him in response, her face blank of any emotion. Since she didn't seem to be up to keeping their conversation running smoothly, he decided to step in and get down to business.

"Why won't you leave him?"

"That was never a part of our arrangement."

"Arrangement?" He let out a bark of laughter, his voice adopting a frigid tone. "You mean this sick game we're playing? Sorry princess, but I'm throwing in my cards."

"Chuck…" "

Save it."

"Cut the act Chuck. Where is this coming from? You were more than content with what we had, no strings attached."

"Well obviously you made a mistake in your evaluation of yours' truly because I never wanted to share you with him."

"Oh, really? Because it sure didn't seem that way when you were off bedding a different girl each and every night of the week."

"You know for a fucking fact that they don't mean a thing to me, Blair."

"Yet you still sleep with them anyways." Her eyes had begun to fill with unshed tears, a habit that she had picked up when arguing with Chuck.

"End your sham of a relationship. Break up with Nate and I promise that you will be the only one that I bed." The end of his statement had taken on a slightly teasing tone, revealing the faith that he had in her, that she would chose him, once and for all.

Every single part of her wanted to take him up on his offer, how desperately she wanted to nod and bury herself in his safe embrace. But no matter how much she wanted him, she just couldn't do it.

Instead of the "yes" that he had been hoping for, she gave a reply that she had long since memorized.

"I just can't…."

"Then I just can't stop seeing Vanessa, it's as easy at that." Chuck's gaze was cold, determined not to let her see how badly she was breaking him.

"Vanessa? Honestly Chuck, if you're going to try to make me jealous, at least pick someone who knows the different between Jimmy Choos and Monalo Blaniks." Blair raised her voice, taking a step closer to him and meeting his gaze with fire in her eyes. Shooting his arm out, he took a hold of her shoulder, pulling her frame flush up against him. With uncommon gentleness he tucked a stray tendril of hair behind her ear and let his breath settle over her responsive skin. She wanted him to kiss her more than anything in the world.

"I'm done with you, Waldorf." He turned on his heel and left her disheveled in the empty hallway, grasping onto the wall for support. Her entire body felt weak from the newly emptied contents and the brutal confrontation with Chuck Bass. Chuck returned to his table and took a seat across from Vanessa. His head was beginning to ache from all the thoughts that had spawned from the argument.

"Back from a quickie in the back closet?" Vanessa joked.

Chuck let out a strained chuckle "Sadly, no."

"Oh, well poor Chuck Bass, don't look _too_ depressed about it." She offered him a small smile, placing her hand over his.

"Although...there is a way you could make it better." He flashed her a devious grin, eyes sparkling with mirth.

"Don't even think about it, buddy."

"We're buddies now?" Vanessa chuckled at his surprise, "Of course."

* * *

"Blair." Serena helped her friend back into her seat, "What happened to you?" Blair looked at her with a weary expression, choosing not to go into her recent argument. 

"Where's Nate?" "He had to go see his parents, an emergency of some sort. He asked me to take you home. Now what happened after I left you in the bathroom?" "Nothing," Blair shook her head profusely, looking back at Serena pleadingly "Can we just get out of here?" "Of course." As soon as they climbed into a cab, Blair leaned against the window, closing her eyes and hoping to forget.

* * *

Chuck walked Vanessa back to her loft, standing in the doorway they smiled politely at one another.

"Thanks for lunch," Vanessa whispered "and the beautiful flowers." Chuck's smile was replaced with a devilish smirk, quickly leaning in for a kiss. To his surprise, she pulled away before he had a chance to plant one on her.

"You don't want this." her voice firm but kind, "Neither do I."

His eyes turned to the floor. "I'm sorry." he mumbled, angry with himself for ruining his relationship with such an amazing girl, and in such a short amount of time.

"Bye Chuck," she kissed him on the cheek before closing her door.

"Wait, do you think I can come in? Hang out? Do what ever it is you Brooklyn people do for fun?" He asked quietly, nervousness leaking through his words.

Vanessa grinned, "Only if you promise to stop trying to bed me."

"You have my word."

"Come on in then." Ushering him into the small loft, she closed the door behind him. "Now for the million dollar question. Do you watch Lost?" Her face tensed in anticipation.

"What's Lost?" He asked, taking a seat on her less than comfortable couch. "Oh, you did not just ask that." She replied dramatically, putting the DVD into her player and turning off the lights. "I'll make an addict of you yet."

This was the beginning of a beautiful friendship, or an amusing one at least.

* * *

"Blair..." 

She turned around quickly in her living room, breathing frantically. She was nervous as hell.

"Nate," her voice cracked, "I didn't think you'd be here so soon. I thought-"

"What's wrong?" He interrupted her, staring intensely with those puppy dog eyes.

Her heart was beating out of her chest. How would she reply? _I love you, let's be together forever, by the way I slept with Chuck? _To the point.Yet too blunt.

"I think we need to break up." She whispered, she felt as if she couldn't breath. The sentenced escaped her lips without a moment of thought. _Fuck. Fuck. Fuck_. What am I doing? She thought to herself.

"Blair...What?" Nate looked confused. He was still staring at her with those bright green eyes, the care and worry were replaced with confusion and shock, "Where the hell is this coming from?"

"I need a break, Nate. From you. From us. I need-" she choked back tears, "I need you to stay away from me." She wanted to scream at him. She wanted to reveal every little detail of her intimate affair with Chuck Bass. She wanted to yell, punch, kick him for being such an ignorant, oblivous...too perfect gentlemen. She wanted to give him a legit reason for breaking his heart. She wanted for him to hold her tight and comfort her. Tell her it will be okay with Chuck. God, that name. She was on the verge of a break down, ruining everything she worked so hard for, for what? Chuck Bass? How stupid was she? Nate kept his eyes on her. The face she knows and loves all too much standing before her, begging for answers was all too much for Blair.

"Dorota, please show Nate out." She wiped away her tears in a frenzy, turning her back quickly to avoid any more confrontations with Nate and rushed up to her room. The unexpected break up, her actions, the past 72 hours of her life flew by in a haze. She tried to make sense of it all. She needed to clear her head. Maybe Breakfast at Tiffany's, a glass of gin and a few sleeping pills will do the trick. Throwing back the drink, she climbs into bed, throws the cover over her body and falls asleep to Audrey Hepburn's voice singing her to sleep. She would fix all this tomorrow. By noon, she will be back with Nate. Move on with her life. Go back to the plan of Yale, Nate, the white picket fence and those 2.5 kids. Nate will surely take her back. Everything will go back to normal. But for tonight, just for one night, she would take a break from her picture perfect life and allow herself to miss Chuck Bass. Just for one night.

* * *

"Serena" 

A surprised Serena Van Der Woodsen tightened the rope around her robe as she opened her door to Nate Archibald pounding on her door.

"Nate...what are you doing here?"

"Blair..." He was desperate, confused and needed answers. Serena would surely know what's going on with her best friend but how would he ask? He wasn't sure where he stood with the gorgeous blonde girl before him. He had never spent time alone with her since he had chosen to commit to Blair.

"Come in." she guided him to the living room. He throws himself onto the loveseat as she hurries to the bar, fixing him a strong drink.

"I'm so sorry about Chuck and Blair...but you have to understand-"

"Wait, what?" He stood up and looked at her questionly.

"Uh...nothing. Never mind what I said." FUCK. Serena thought to herself. She messed up big time.

It's a shame they've alll known each other all their lives. Because Nate could always tell when Serena was lying, he knew her all too well. The only two other people he knew that much about were Chuck and Blair, which would explain...everything was falling into place.

"They have something going on, don't they?" he raised his voice, and Serena was overtaken by fear, "Is that why she broke up with me?"

"She broke up with you?"

"Answer the fucking question." he demanded agressively, taking a step towards her and shaking her fragile body harshly.

"Nate, it's in the past. It was stupid, it's over." Serena was begging him to believe her. She knew it was too late as he rushed out the door. Surely to find Chuck.

"Fuck. Fuck. Fuck." she mumbled over and over to herself, pacing around frantically. She struggles to dial the memorized numbers on her phone. When Blair's phone goes straight to voicemall, Serena realizes it's too late. She grabs her goat and rushes out the door.


	10. Chapter 10

Chuck cursed as he was awoken by the loud pounding on his door.

"Nathaniel? What's-?

Chuck was short when Nathaniel grabbed him by the collar and pinned him against the wall.

"Did you screw her Chuck?" Nate spat out.

"I don't know what you're talking about."

"Blair!" Nate screamed, "Did you screw around with her?"

"Nate-"

"Don't lie to me Chuck!" he let go of his grip but stared at Chuck all the same.

After a lifetime of silence, Chuck's gaze just turned to the ground, a look of defeat spread across his face. "It's not-...It wasn't-"

"Son of a bitch!" Nate threw a punch across Chuck's face, "Of all the girls you could screw around with, Blair? You sick bastard."

Nate threw more punches at Chuck, who refused to fight back.

"Nathaniel! I didn't mean-"

"How long Chuck?" Nate threw Chuck across the room against the bar. The glass of whiskey shattered on the floor "How long were you screwing around with my girlfriend?"

"It was a one time thing!" Chuck lied, "A mistake."

"Don't fuckin lie to me Chuck!" Nate yelled, throwing a glass ashtray towards Chuck.

The ashtray hit the mirror behind the bar and both objects crashed into pieces.

"She wouldn't have broken up with me if you two didn' t have something going on."

Chuck's eyes shot up at Nate's, "She broke up with you?"

"Answer the question you fuck. For how long have you been lying to my face?" Nate repeated, "You cheating scumbag, I was your friend when you had nothing. How could you do this to me? You don't even have the decency to tell me how long you've-"

"Nathaniel! Don't do this." Chuck pleaded.

"Jesus christ Chuck, I understand that you find sick pleasures in screwing woman over because your slut of a mom left you to rot with your douchebag of a father but Blair?"

Chuck had had enough. He lunged across the room shoving Nate backwards against a wall, sending paintings to the ground.

"Three months! Is that what you wanted to hear? I've been fucking you girlfriend behind your back now for three months."

"You sick bastard!" Nate knocked Chuck to the ground, hitting him over and over again until deep cuts were formed across Chuck's face.

"From now on you stay the hell away from me. I'm done with you." Nate declared, before leaving Chuck's suite abruptly.

"Blair!" Serena shouted, running up the marble stairs.

"Serena, what is it?" Blair Waldorf stood in her room drying her damped hair.

"I tried calling you-"

"I was in the shower."

"Nate knows." Serena says flatly.

"What?" Blair threw aside the towel, "What do you mean he knows? He knows about what?"

"We need to go. Chuck's. Nate seemed really angry." Serena spat out impatiently.

Without another word, Blair hurried after Serena out the door and into the awaiting cab.

Chuck laid motionless on his floor as Vanessa entered his room moments later.

"Chuck?" She gasped, "What the hell happened?"

She helped him over to his couch and knelt down beside him, tracing her fingers gently over his wounds.

"I just saw Nate in the hallway, did he do this to you?"

Chuck didn't reply but simply answered with a smirk.

"We need to get you to a hospital."

"It's fine." Chuck mumbled, wincing at her touch.

"No it's not. Look at yourself!" Vanessa's voice broke as tears were flowing from her cloudy eyes, "Where's your first aid kit?"

Chuck just slightly shook his head.

Vanessa sighed, "Of course you wouldn't have one. Here, let's get you into bed."

After much difficulty of getting Chuck undressed and into bed he was already fast asleep.

"Blair..." he mumbled in his slumber

"Damnit Chuck, what did she do to you?"

Vanessa slipped out to retrieve a few items to clean Chuck's wound when she spotted Serena and a frantic, underdressed Blair Waldorf at the end of the Palace hallway.

"Vanessa!" Serena exclaims.

"What are you doing here?" Blair questioned.

"I think the question is what are you doing here." Vanessa fired back, "You've done enough damage in a day, don't you think?"

"Chuck, is he okay?" Blair asked.

"He will be if you keep that lunatic boyfriend of yours away from him."

"I need to see Chuck-" Blair pushed pass Vanessa only to be stopped.

"No, what you need is to understand that I'm Chuck's girlfriend now. Whatever the two of you had is over. Is that clear enough? The world does not revolve around you Blair Waldorf, and neither does Chuck Bass. So why don't you do us all a favor and stop playing your sick little games and keep your pyscho boyfriend away from Chuck." Vanessa raised her voice.

"What did Nate do? I just need to see Chuck." Blair pleaded, eyes filled to the brim with unshed tears.

"As far as I'm concerned, Chuck wants nothing to do with you." Vanessa replied coldly.

"Blair, honey." Serena helped her friend turn around and walk away, giving Vanessa an icy cold stare.

"He wants nothing to do with me." Blair repeated in the cab hysterically, "How did Nate know, Serena? How did Nate find out? Did Chuck tell him? Does he not care about me anymore?"

"Blair, honey, it's alright. Everything will be okay" Serena held onto her friend, afraid of revealing the truth at a time like this.

"Nathaniel? Where have you been? I've been trying to find you all night." The Captain scrowled as Nate entered his office.

"Mom said you wanted to see me?"

"Why do you look like hell?"

"I- I had some business to take care of." Nate replied.

"Nate, you're an Archibald, you cannot be doing anything stupid to risk destroying our reputation."

"I know Dad." Nate sat down across from The Captain.

"What I wanted to talk to you about was your proposal with Blair."

"What?"

"Your mother and I were talking and we think it's best if you propose to Blair as soon as possible. Seeing your history, it's only a matter of time."

"I can't do that. I will not marry her."

"Why the hell not?"

"She slept with Chuck, Dad!" Nate yelled, "My best friend? Remember him? She slept with Chuck behind my back for three months. Playing me like a complete fool. As far as I'm concerned, I never want to see either of them again."

"Chuck Bass? That new money?" The Captain asked, astonished, "You idiot, how could you let it go on for that long and not know?"

He threw the nearest book across the desk, hitting papers and staplers onto the floor.

"Damnit Nate. Why can't you even hang onto Blair Waldorf? That's all we asked of you."

"Dad..." Nate started.

"Are they still seeing each other?" The Captain asked.

"What?"

"Blair and Chuck."

"No, I don't think so."

"Does anyone else know about them?"

"What? No, just Serena and I. Dad, what are you-"

"You need to propse to her. Take her back. I'm sure it was just a phase. Pretend you're over it."

"Dad, I'm not! She went behind my back." Nate shouted.

"I said pretend, didn't I?" The Captain raised his voice, "Nate. Do you know what the Waldorf name can do for us. Blair loves you, if you take her back she'll certainly never dare to wrong you again."

"I can't..."

"Nate, we will lose everything if you don't do this."


End file.
